HU200079B - Herbicides containing derivatives of 2-/metoxi-carbonil/-benzosulphonil-carbamid - Google Patents

Abstract

The compound 2-[N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N-methylaminocarbonyl] amino-sulfonyl] benzoic acid, methyl ester and its agriculturally suitable salts is a potent herbicide having excellent utility for selective weeding of wheat and barley.

Description

The present invention relates to a herbicidal composition which contains as active ingredient a very strong herbicidal composition with a low residual 2- (methoxycarbonyl) nasol sulfonylurea stem coating.

2- The active ingredient, the 2-methoxycarbonylbenzenesulfonylcarbamide derivative, is an active ingredient of the composition of the present invention.

It is well known that there is a continuing demand from agriculture for herbicidal active ingredients which are highly active, yet have high selectivity and low residual activity against important crops such as cereals.

The important role of cereals in the diet of mankind is also well known. However, it is also known that many of the known herbicidal active ingredients have a high residual activity, with the consequence that crop rotation with crop plants is not readily accomplished in areas where the herbicidal active ingredient is present, there is a need for high potency but low residual herbicidal agents.

It has been found that 2 - {[N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylamino) m.p. 146-148 ° C. -carbonyl)] - aninosulfonyl} benzoic acid methyl ester far meets the above requirements and can therefore be used and used as an active ingredient in highly valuable herbicidal compositions for selective post-emergence weed control, especially in cereals such as wheat and barley. The compound of formula (I) is rapidly degraded in soil and, under normal conditions, there is no crop which could not be grown later in the area where the compound of formula (I) was previously grown. We were used.

Λζ Compound of formula (I) as shown in Scheme A, 2- (methoxycarbonylbenzenesulfonyl isocyanate of formula (TI) and 2-methoxy-4-methyl-6- (methylamino) of formula (III) The reaction is conveniently carried out in an inert aprotic organic solvent such as dichloromethane, 1,2-dichloroethane, tetrahydrofuran or acetonitrile at a temperature between 20 ° C and 85 ° C.

Preparation of starting isocyanate of formula (II). U.S. Patent No. 4,394,506. The preparation of aminotriazine (III) by Tsujikawa, T. et al., Yakugaku Zasshi. .95. 512 (1975) or Japanese Patent Application 217710000 (Chemical Abstracts, 6-1, 14200 g, 1900).

The following examples and the experimental part serve to better illustrate the invention.

l. example

2-yl N- (4-MeThoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonyl) -1-amino-10-yl-phenyl-benzoic acid methyl ester

To a solution of 22.4 g (93.0 mmol) of 2-methoxycarbonylbenzenesulfonyl isocyanate in 100 mL of dichloromethane was 10.7 g (69.6 mL15 mmol) of 2-methoxy-4-methyl-6 - (methylamino) -1,3,5-triazine followed by catalytic amount of 1,4-diaza (2,2,2) bicyclooctane. After stirring under nitrogen at room temperature overnight, the reaction mixture was concentrated in vacuo and the residue was triturated with diethyl ether and then washed with 1-chlorobutane. 27.8 g of the title compound are obtained in the form of a white powder, m.p. 126-131 ° C.

IR (KBr) 1735 (C = 0), 1720 (C = 0), 1570, 1470, 1430, 1350 (SO2), 1285, 1270, 1170

(SO) and 1160 ^cm-first Nuclear Magnetic Resonance Spectrum (CDCl 3 / DMSO) ¹ ' delta: 2.7 (s, HET-CIb) 3.4 (s, N-Clb) 3.9 (s, COzCHa) 4.05 (s, HET-OCHa) 7.35 to 7.75 (m, ArH) 8.15-8.4 (m, ArH) 14.0 (broad, NH).

1) CDCl = deuterochlorophore

DMSO = Dimethylsulfoxide When carried out as described above, but with a smaller reaction volume and addition of xylene to the reaction mixture, the title compound precipitates as a white powder, m.p. 146-118 ° C.

The compounds of formula (I) are used in the form of preparations which are prepared in a conventional manner. Examples of such compositions of the invention include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, and the like. They are. Some of these formulations are directly applicable. Sprayable formulations may be diluted with an appropriate medium and applied in a spray volume of a few liters / hectare to a few hundred liters / hectare. The high active ingredient formulations are used primarily in the preparation of other formulations. The agrochemical compositions of the present invention contain from 0.1 to 95.0% by weight of the active ingredient of the formula I and at least one of the following:

a) 0.1-20 wt.% surfactant (s), ^{oh :?}

b) 1-99.9 wt.% solid or liquid carriers).

In particular, the compositions of the invention contain the active ingredient and other ingredients in the composition of Table I.

f. spreadsheet

agent Weight% 'Carrier! OK) Felülctaktiv materials) wettable powder preparations 20-90 0-74 1-10 oily suspensions, emulsions, solutions (including emulsion solutions) also concentrate) 3-50 40-95 0-15 aqueous suspensions 10-50 40-84 1-20 dusts 1-25 70-99 0-5 granules and pellets 0.1-95 5-99.9 0-15 high in active ingredient products 90-95 0-10 0-2

+ the active ingredient, together with the surfactant and / or the carrier, together constitute 100% by weight

The composition may also contain different amounts of the active ingredient, depending on the use of the composition and the physical characteristics of the active ingredient. In some cases, it may be desirable to have a higher surfactant to drug ratio. This can be achieved by adding more surfactants to the composition or by adding an additional amount of surfactant immediately before use.

Some typical solid carriers are described in Watkins et al., 2nd edition of the Handbook of Insecticide Duel Diluents and Carriers (published by Dorlands Books, Caldwell, New Jersey), but other mined or manufactured solid carriers may also be used. Solid carriers with good absorption properties 45 are preferably wettable powder formulations, while solid carriers with less good absorption properties can be used in the preparation of powders. Typical carriers and solvents useful in the compositions of the present invention are described in Marsden's .Solvents Guide (2nd edition, published by Interscience, New York, 1950). Preferably, slurry concentrates may be prepared in a solubility below 0.1% by weight, and the solution concentrates are preferably stable at 0 ° C for phase separation.

Suitable surfactants for θθ and their recommended applications are described in: McCutcheon's Detergents and Emulsifiers Annual '(MC Publishing Corp., Ridgewood, New Jersey) and edited by Sisely and Wood. Encyclopedia of Surface Active Agents (Chemical Publishing CO., Inc., New York 1964). The compositions may also contain minor amounts of other additives, such as antifoaming agent, antifouling agent, antimicrobial agent and anticorrosive agent.

The compositions of the invention may be prepared in a known manner. Solutions are prepared by simply mixing the ingredients. Fine-grained solid compositions can be prepared by mixing and then generally milling. Grinding can be carried out, for example, in a hammer mill or in a liquid power mill. The suspensions may be prepared by wet milling (see, for example, U.S. Patent No. 3,060,084). Granules and pellets may be prepared by spraying the active ingredient on a granular carrier or by agglomeration techniques (see Chemical Engineering, Dec. 4, 1967, p. 147 ff., By J, E. Browning, and Perry's Chemical). Engineering's Handbook '4th Edition, pp. 8-59, published by McGraw-Hill New York in 1963).

The preparation of preparations is further described in the following literature:

Column 6, line 16, column 7, line 19, and U.S. Pat. examples;

U.S. Patent No. 309,193, column 5, line 43, column 7, line 62, and 8, 12, 15, 39, 41, 52, 53, 132, 138 - Examples 140, 162-164, 166, 167 and 169-182;

U.S. Patent No. 891,855, Column 3, Line 66, Column 5, Line 17, and Columns 1-4. examples;

G. C. Klingman, .Weed Control as a Science ', 81-96. pages, publisher; John Wiley and Sons, Inc., New York, 1961;

J. D. Fryer and S. A. Evans, The Weed Controi Handbook, 5th Edition, 101-103. page, published by Blackwell Scientific Publications, Oxford,

In a double tapered mixer, a slurry of the wettable powder formulation containing about 25% by weight of the active ingredient is sprayed onto the surface of the attapulgite particles, and the particles are dried and packaged.

Example 5

1968th 10 Extruded pellets In the examples below, if nothing else percentages are by weight component Quantity lölnek. 2- [N- (4-Methoxy-6-methyl-1,3,5 -triazin-2-yl) -N- (methylamino) 15 -karboniU amino szuifonili- Example 2- benzoic acid methyl ester 25% anhydrous sodium sulfate 10% Wettable powder formulation crude calcium lignin sulphonate 5% sodium alkylnaphthalenesulfonate 1% component Quantity 20 calcium magnesium bentonite 59% 2 - {[N- (4-methoxy-6-methyl-3,5- The components are mixed together, triazin-2-yl) -N- (methylamino ground in a fine mill and about 12% by weight - carbonyl 1] -aminosulfonyl} - moisten with water. thereafter the resulting benzoic acid methyl ester 80% bones of about 3 mm in diameter cylindrical sodium alkylnaphthalenesulfonate 2% 25 strips are extruded and then < foals 3 mm Sodium ligninsulfonate 2% pellets of around length cut it. These synthetic amorphous then immediately after drying, silica 3% can be used or broken, kaolinite 13% to pass through a sieve with a mesh size of 0.84 mm. The components are mixed and then 30 In the latter case, the 0.42 mm grind in a hammer mill until a material remaining for use particle size is essentially 50 micrometers wrap until the finer material decrease. Then we stir again. recycled. Example 3 35 Example 6 Wettable powder formulation Oily suspension component Quantity 40 component Quantity 2- {lN- (4-methoxy-6-methyl- 2- [N- (4-methoxy-6-methyl-3,5- l, 3,5-triazin-2-yl) -N- triazin-2-yl) -N- (methylamino - (methylaminocarbonyl) J- carbonyl-amino-sulfonyl] - aminosulfonyl benzoic acid benzoic acid methyl ester 25% methyl ester 50% 45 poly (oxyethylene) - sodium alkylnaphthalenesulfonate 2% sorbitol hexaoleate 5% low viscosity methylcellulose 2% large amounts of aliphatic diatomaceous earth 46% component The components are mixed and then hydrocarbon oil 70%

in a hammer mill it is subjected to coarse grinding and then in a milling mill to fine grinding until the particle size drops substantially below 10 micrometers. Then we stir again.

The components are ground in a sand mill until the solid particles have a particle size of less than about 5 micrometers. The resulting suspension can be used directly, but is preferably further diluted with oils or emulsified in water.

Example 4

Granular preparation

Component Amount of wettable powder composition according to Example 3 5% attapulgite granules (0.42-0.84 mm particle size) 95%

-47. example

Moisturizing face preparation

Example 10

component

2- [N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonylaminosulfonyl] benzoic acid methyl ester sodium alkyl naphthalenesulfonate sodium lignin sulphonate low viscosity methyl cellulose attapulgite

The components are mixed and ground in a hammer mill until the particle size 15 drops below substantially 100 micrometers. The powder is then passed through a 0.3 mm mesh sieve prior to packaging.

Quantity

20%

4%

4%

3%

69%

Solution

Component Quantity

2- [N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonyl-D-aminosulfonyl] -benzoic acid methyl ester 5% water 95 %

The components are combined and mixed until a solution is obtained. It can then be packaged for use.

Example 11

Low active ingredient granular preparation

component Quantity Example 8 2- [N- (4-methoxy-6-methyl-3,5- -triazin-2-yl) -N- (methylamino- Low active ingredient granular carbonyl) amino-sulfonyl] - ling 25 benzoic acid methyl ester 0.1% 0.42-0.84mm component Quantity attapulgite granules 99.9% 2- [N- (4-methoxy-6-methyl-3,5- In a double tapered mixer a dust -triazin-2-yl) -N- (methylamino- spray on the surface of attapulgite particles carbonyl-amino szulfonilj- 30 and then evaporate the solvent. benzoic acid methyl ester 1% the material is cooled and pack- N, N-dimethylformamide 9% Juk. 0.42-0.84mm attapulgite granules 90% Double tapered mixer the dust was removed 35 Example 12 attapulgite granules surface spray with solution of the active ingredient and then the mixer for a short time Granular preparation let it spin and the preparation, goals. component Quantity 40 2- [N- (4-methoxy-6-methyl-3,5- triazin-2-yl) -N- (methylamino Example 9 carbonyl) amino-szulfonilj- benzoic acid methyl ester 80% Aqueous suspension humectants 1% 45 crude lignin sulphonate salt component Quantity (5-20% natural 2- [N- (4-Me Toxic-6-methyl-1,3,5- contains sugar) 10% - triazin-2-yl) -N- (methylamino- attapulgite substance 9% carbonyl-amino-sulfonyl] - The components are mixed and then benzoic acid methyl ester 40% 50 we grind it so that 149 micrometers polyacrylic acid thickener 0.3% pass through a sieve. THE received little dodecyl-phenol-poly- then the fluid bed granulator (Ethylene glycol ether) 0.5% feed, then the price of fluidizing air disodium phosphate 1% the mixture is weak monosodium phosphate 0.5% 55 in a fluid state while stirring be. THE polyl vinyl alcohol) 1% water into a thin stream of fluidized material water 56.7% sprayed. Fluidization and e i spraying

The components are mixed and then ground in a sand mill until the size of the solid particles is substantially less than 5 micrometers.

continued until the granules reach the desired size. The spraying is then interrupted, but fluidization is continued (optionally with heating) until the water content falls below the desired value, generally below 1%. The material is then removed from the fluidizing device to the desired grain size, with 149 micrometres and 1410 micrometres.

HU 200079 Β microns and is packaged as a last resort.

Oily suspension

Example 13

component

2- [N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonyl-1-aminosulfonyl] -benzoic acid methyl ester in the form of aerogel silicon Synthetic amorphous silica

component

2- N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonylamino-sulfonyl) -benzoic acid methyl ester polyalcohol carboxylic acid esters and oil soluble a mixture of petroleum sulfonates xylene

Quantity

35%

6%

59%

Leave an active ingredient-containing preparation

Quantity .95%

2.5% 15

2.5%

After mixing, the components are ground in a hammer mill until the total amount of material passes through a 0.3 mm 20-mesh sieve. The composition thus obtained can be used primarily for the preparation of another composition ready for use.

The components are mixed and the mixture is ground in a sand mill until the particle size drops below 5 micrometers. The product thus obtained can be used directly, diluted with oils or emulsified in water.

Example 17

dusts

Example 14

Wettable powder formulation

Component Quantity

2- (N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonyl) amino-sulfonyl] -30

Benzoic Acid Methyl Ester 90% Dioctyl Sodium Sulphosuccinate 0.1% Synthetic Fine-grained Silica 9.9%

The components are mixed and then ground in a hammer mill until a

Component Quantity

2- [N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (methylaminocarbonyl) amino-sulfonyl] -benzoic acid methyl ester 10% attapulgite 10 % Pyrophiles 80%

The active ingredient is mixed with attapulgite and ground in a hammer mill until the particle size is substantially less than 200 micrometers. The concentrate thus obtained is mixed homogeneously with powdered pyrophyllite.

The compound of formula (I) may be used in combination with the following herbicidal agents:

the particle size is essentially below 100 micrometers. The powder is then passed through a 0.3 mm mesh sieve prior to packaging.

Example 15

Wettable powder formulation

component Quantity 2- [N- (4-methoxy-6-methyl-3,5- - triazin-2-yl 1-N- (methylamino- - carbonyl) -aminosulfonyl] - benzoic acid methyl ester 40% Sodium lignin sulfonate 20% montmorillonite 40% The components thoroughly mix up-

and then first grind in a hammer mill and then in a mill mill until the particle size drops to substantially less than 10 microns. Stir again before packing.

2,4-D fluorochloridone 2,4-DB fluoroxypyr in bar glyphosate basagran imazaquin bentazone ioxynil benzoylpropethyl isoproturon bifenox L-flampropisopropyl bromofenoxium linuron bromoxynil Lontrel butraline MCP chlometexynil MCPA chlorfenprop- -methyl MCPB clepyralid (3,6-DCP) mecoprop (MCPP) chlorsulfuron methabenzthiazuron chlortoluron metoxuron cyanazine metribuzin

diallate dicamba disclorprop (2,4-DP) diclofop-methyl difenzoquat dinoseb (DNBP) metsulfuron methyl neburon nitrofene paraquat pendimethaline

-611

HU 200079 Β dinoterbe diquat diuron picloram propanil

TBA

DNOC terbutryn flainprop isopropyl triallate flamprop methyl trifluraline

Methyl 3-methyl-6- (4,5-dihydro-5-methyl-5- (1-methylethyl) -4-oxo-1H-imidazol-2-yl) benzoate,

3 - (((4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonylamino-sulfonyl} -2-thiophenecarboxylic acid methyl ester,

4-Chloro-2 - ([(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -athinocarbonyl] -aminosulfonyl} -benzoic acid (1-methyl-ethyl) )-ester

Most preferably, it may be used in combination with any of the following compounds:

3- {4- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -amino-sulfonyl} -2-thiophenecarboxylic acid methyl ester;

3-methyl-6- [4,5-dihydro-5-methyl-5- (l-methylethyl) -4-oxo-lH-imidazol-2-yl-benzoic acid methyl ester;

difenzoquat; or diclofop-methyl.

The composition of the invention can thus be used for postemergent weed control in cereals such as wheat and barley. The composition can control a broad spectrum of broadleaf weeds, while being exceptionally safe against crop plants. Because its active ingredient is rapidly distributed in the soil, it can be used where double sowing is possible or where, after the crop, a crop which is sensitive to the currently known herbicidal agents is desired.

The application rates range from 8 g / ha to 125 g / ha. The utilization rate used in a particular case depends on factors such as the nature and state of development of the weeds to be controlled; the nature of the crop; climatic conditions; the form of the composition used and the nature of any other herbicidal agent which may be added. It is not a problem for one of ordinary skill in the art to determine the application rate to be used in a particular case.

The herbicidal composition containing the compound of formula (I) may also be used in combination with other sulfonylureas, diaryl ethers, ureas, triazines and carbamates which are selective for cereal crops.

The herbicidal activity of the compound of formula (I) is demonstrated in the following greenhouse experiments.

Polyethylene-coated plastic dishes are filled with pasteurized paste at pH 6.5 with 1 wt.

-ΊSassafras with clayey-sandy soil. Wheat (Triticum sativum), barley (Hordeum vulgare, wild bean (Avena fatua), Bromus secalinus, Alopecurus myosuroides, Poa annua, Setaria viridis, Loliutn multiforum and rapeseed (Brassica nap) are planted in one bowl ) The second bowl was planted with Matricaria inodora, Galium aparine, Salsola kali, Capsella bursa-pastoris, Kochia scoparia, Solanum nigrum, Veronica persica, Poiygonum convulvulus and sugar beet ( Beta vulgar) For postemergence treatment, the first bowl is planted 14 days prior to spraying and the second bowl 24 days before spraying. and wild oats are in the bivalve state of development (Zadok's condition 11) Similarly, two additional bowls are prepared before spraying to perform preemergent treatments. ldat containing 12% by weight of active ingredient, 60% by weight of acetone, 12% by weight of water, 12% by weight of glycerol and 4% by weight of Tween 20 (20 moles of ethylene oxide sorbitan monooleate), and with a belt sprayer.

Additionally, three species are evaluated: Veronica hederaefolia, Stellaria media, and Viola arvensis. These seedlings grow in pots of 12.5 cin filled with soil of the aforementioned quality. The plants were planted 22 days before treatment. The herbicidal treatment is carried out in the same way as for the bowls.

After treatment, the plants are grown in a greenhouse for 21 days, when visual evaluation is performed by comparison with untreated control. The following extreme scale is used for the evaluation:

= no effect and 100 = total extinction

II. spreadsheet

Application rate (g / ha) t Compound of Formula I] 125 64 32 16 8 4 2 preemergence wheat 0 0 0 0 0 0 0 barley 0 0 0 0 0 0 0 sugar beet 100 100 80 80 60 50 20 rape 90 80 60 40 20 0 0 wild oats 0 0 0 0 0 0 0 Bromus secalinus 0 0 0 0 0 0 0 Alopecurus myosuroides 30 0 0 0 0 0 0 Poa annua 20 0 0 0 0 0 0 Setaria viridis 0 0 0 0 0 0 0 Lolium multiforum 0 0 0 0 0 0 0 Matricaria inodora 50 40 20 0 0 0 0 Galium aparine 20 0 0 0 0 0 0 Saisola kali 90 80 80 30 0 0 0 Capsella bursa-pastor 90 80 70 70 30 20 0 Kochia scoparia 80 70 40 20 0 0 0 Solanum nigrum 80 70 30 20 0 0 0 Veronica persica 90 60 40 40 0 0 0 Polygonum convolvulus 70 60 20 0 0 0 0 postemergence Wheat 0 0 0 0 0 0 0 barley 0 0 0 0 0 0 0 sugar beet 100 100 100 100 100 100 90 rape 100 100 100 100 100 90 80 wild oats 0 0 0 0 0 0 0 Bromus secalinus 0 0 0 0 0 0 0 Alopecurus myosuroides 40 20 0 0 0 0 0 Poa annua 30 20 0 0 0 0 0 Setaria viridis 70 40. 0 0 0 0 0 feathers multiforum 0 0 0 0 0 0 0 Metricaria inodora 100 100 100 90 80 60 50 Galium aparine 70 50 30 20 0 0 0 Salsoia potassium 100 100 100 100 90 90 70 Capsella bursa-pastor 100 100 100 100 90 90 80 Kochia scoparia 100 100 100 100 80 70 50 Solanum nigrum 90 80 80 70 60 60 50 Veronica persica 100 90 80 70 50 30 30 Polygonum convolvulus 90 90 80 70 70 30 0 Veronica hederaefolia 0 0 0 30 0 0 0 Viola arvensis 95 90 90 85 65 50 0 Stellaria media 100 100 100 95 95 80 75

-815

II. Continuation of Table II / Known compound, 2- {1N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (aminocarbonyl)] - aminosulfonyl} -benzoic acid methyl -ester/

Application rate (g / ha) 125 61 32 16 8 preemergence wheat 40 10 0 0 0 barley 80 70 50 50 20 sugar beet 100 100 100 100 100 rape 100 100 90 90 80 wild oats 80 80 50 30 20 Bromus secalinus 80 80 70 50 30 Alopecurus myosuroides 80 70 50 30 20 Poa annua 70 70 50 30 10 Setaria viridis 70 60 30 20 0 Lolium multiforura 90 90 80 70 30 Matricaria inodora 90 90 90 80 80 Galium aparine 80 70 60 50 30 Salsola kali 90 90 80 80 80 Capsella bursa-pastor 100 100 90 90 90 Kochia scoparia 100 100 90 90 80 Solanum nigrum 90 90 80 80 70 Veronica persica 90 90 90 80 80 Polygonum convolvulus 90 90 90 90 70

II. Continuation of Table II / Known compound, 2-1- (N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N- (aminocarbonyl) -1-aminosulfonyl} -benzoic acid methyl ester /

Application rate (g / ha) 125 64 32 16 8 preemergence wheat 60 40 20 0 0 barley 80 70 50 20 0 sugar beet 100 100 100 100 100 rape 100 100 100 100 100 wild oats 70 70 50 20 0 Bromus secalinus 90 80 70 50 50 Alopecurus myosuroides 90 70 60 40 20 Poa annua 90 70 70 30 20 Setaria viridis 80 60 50 20 0 Lolium multiforum 90 90 70 50 30 Matricaria inodora 100 100 100 100 100 Galium aparine 80 80 70 40 20 Salsola kali 100 100 90 90 90 Capsella bursa-pastor 100 100 100 100 90 Kochia scoparia 100 100 100 100 100 Solanum nigrum 100 100 90 70 70 Veronica persica 100 100 100 90 80 Polygonum convolvulus 100 90 90 90 80 Veronica hederaefolia 50 50 50 50 40 Viola arvensis 100 100 100 100 100 Stellaria media 100 100 100 100 95

-917

II. Continuation of Table II / Compound of Formula I and 3 - {[(4-methoxy-6-diethyl-1,3,5-triazin-2-yl) -aninocarbonyl) -aminosulfonyl} -2-thiophene- 2: 1 by weight mixture of methyl carboxylic acid /

Application rate (g / ha) 125 64 32 16 8 4 Preeniergens barley (spring) 30 20 0 0 0 0 barley (autumn) 60 30 10 0 0 0 Solanum nigrum 70 70 70 70 60 0 Alopecurus myosuroides 70 70 60 30 20 0 Poa annua 70 70 60 50 30 10 Galium aparine 100 90 90 70 70 20 Broinus secalinus 70 50 40 20 0 0 Bromus tectorum L. 70 50 40 30 20 0 Thlaspi arvense L. 100 100 100 90 90 70 Viola estimates Murr. 100 100 100 90 90 60 Setaria viridis 20 20 0 0 0 0 Loiium multiflorum 70 70 40 40 30 20 Aegilops cylindrica Hóst 100 100 100 100 100 80 Kochia scoparia 20 0 0 0 0 0 Chenopodium album 100 100 100 100 90 60 Veronica persica 100 100 100 100 90 70 rape 100 100 100 100 90 20 Salsola kali 100 100 100 100 100 100 odorless chamomile 100 100 90 90 60 30 sugar beet 100 100 100 100 100 90 wheat (spring) 20 0 0 0 0 0 wheat shoots) 20 20 0 0 0 0 Polygonum convolvulus 100 100 100 100 90 70 wild oats 0 0 0 0 0 0

II. Continue Table

/ compound of formula (I) and 3 - {[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] • carbonyl · amino-sulfonic -phenyl)} -2-thiophenecarboxylic acid ethyl ester 2: 1 weight ratio mix / Rate of use 125 64 32 16 8 4 (G / ha) postemergence barley (spring) 0 0 0 0 0 0 barley (autumn) 0 0 0 0 0 0 Solanum nigrum 90 80 70 70 20 10 Alopecurus myosuroides 50 30 20 0 0 0 Poa annua 50 30 0 0 0 0 Galium aparine 70 50 30 0 0 0 Bromus secalinus 0 0 0 0 0 0 Bromus tectorum L. 0 0 0 0 0 0 Thlaspi arvense L. 100 100 100 90 100 80 Viola estimates Murr. 100 90 100 80 70 40 Setaria viridis 30 10 0 0 0 0 Loiium multiflorum 40 20 10 0 0 0 Aegilops cylindrica Hóst 80 50 50 20 30 20 Kochia scoparia 0 0 0 0 0 0 Chenopodium album 100 90 - 50 50 20 Veronica persica 80 80 60 50 20 0 rape 100 100 90 90 80 80 Salsola kali 90 100 90 50 20 0 odorless chamomile 100 100 90 80 70 50

-1019

Application rate (g / ha) 125 64 32 16 8 4 sugar beet 100 100 100 100 100 100 wheat (spring) 0 0 0 0 0 0 wheat (winter) 0 0 0 0 0 0 Polygonum convolvulus 90 - 70 30 30 30 wild oats 0 0 0 0 0 0

PATENT CLAIMS

Claims (7)

CLAIMS 1. A herbicidal composition comprising, as active ingredient, 0.1 - 95% by weight of 2 - {[N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ) -N- (methylaminocarbonyl) -N-aminosulfonyl} benzoic acid methyl ester, solid and / or liquid diluents and / or carriers customary in the manufacture of pesticides, preferably natural or artificial silicates, clay minerals, water, hydrocarbons, and surfactants, preferably ionic or nonionic emulsifiers or dispersants, and optionally 0.25-0.75 parts by weight of a known herbicidal thiophene derivative, preferably 3 - {per 1 part by weight of the compound of formula (I). With (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] amino sulfonyl} -2-thiophenecarboxylic acid methyl ester. A composition according to claim 1 in the form of a wettable powder formulation comprising 20 to 90% by weight of the active ingredient, optionally up to 0-74% by weight of carrier, and 1 to 10% by weight of a surfactant. 3. A composition according to claim 1 in the form of an oily suspension, emulsion or solution, characterized in that it contains from 3 to 50% by weight of active ingredient, 40 to 95% by weight of carrier and 15% to 15% by weight of surfactant. A composition according to claim 1 in the form of an aqueous suspension, characterized in that it contains 10-50% by weight of active ingredient, 40-84% by weight of carrier and 1-20% by weight of a lethal substance. 5. A composition according to claim 1 in the form of a powder, characterized in that it contains from 1 to 25% by weight of active ingredient, 70 to 99% by weight of carrier and 0-5% by weight of surfactant. Contains 25 substances. G. The composition according to claim 1, in the form of granules or pellets, characterized in that it contains from 0.1 to 95% by weight of active ingredient, from 5 to 99.9% by weight of carrier and 0 to 15% by weight. Contains 30 surfactants. The composition of claim 1 in the form of a high active ingredient composition comprising 90-95% by weight of active ingredient, 0.5-10% by weight of carrier and 35% to 2% by weight of surfactant. 8. Composition according to any one of claims 1 to 3, characterized in that the further herbicidal agent is 3 - {[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] 40-aminosulfonyl] Contains methyl 2-thiophenecarboxylic acid.